A commercially important preparation of an alpha-olefin (also known as α-olefin and 1-olefin) product involves a step of reacting an internal olefin (i.e., a carbon chain comprising a functional group motif, C—C═C—C) with an aluminum alkyl and an isomerization catalyst to form a trialkyl aluminum compound. The trialkyl aluminum compound comprises three alkyl groups, at least one of which is a primary alkyl derived from the internal olefin. (Here a primary alkyl refers to a carbon chain comprising a functional group motif, —CH2—C—C—C wherein the CH2 carbon is bonded to the aluminum). In another step, the process allows the trialkyl aluminum compound to react with a sacrificial 1-olefin and a displacement catalyst so as to displace the primary alkyl derived from the internal olefin from the trialkyl aluminum compound and thereby form the alpha-olefin product. The isomerization and displacement catalysts may be the same or different and typically comprise nickel. Alternatively, the displacement reaction may be run without catalyst at elevated temperature with short residence time in the presence of excess of a sacrificial 1-olefin to generate the alpha-olefin.
The trialkyl aluminum compounds having at least one primary alkyl may also be prepared directly from the alpha-olefin. As such, the trialkyl aluminum compounds are also useful intermediates in preparations of primary alcohols and certain other functionalized derivatives of the primary alkyl such as hydroformylated derivatives.
U.S. Pat. No. 2,959,607 mentions a method of forming a trialkyl aluminum compound containing at least one 1-octyl group by reacting oct-2-ene and aluminum tris(1-methylpropyl) in the presence of cobalt chloride catalyst. Also mentioned is converting the trialkyl aluminum compound to 1-octanol by oxidation and hydrolysis.
U.S. Pat. No. 5,124,465 mentions a method of preparing a linear 1-olefin (i.e., linear alpha-olefin) from an internal olefin via a trialkyl aluminum compound in which at least one alkyl group is a primary alkyl derived from the internal olefin. Also mentioned are certain cobalt salts or complexes.
PCT International Patent Application Publication Number WO 2006/005762 A1 mentions dimerizing linear alpha-olefins to give an internal olefin dimer, and converting the internal olefin dimer to a 1-olefin using a process analogous to that referenced above. Also mentioned are certain cobalt salts or complexes such as, for example, 2-[1-(2-tertiary-butylphenylimino)ethyl]-6-[1-(4-eicosanoxy-3,5-diphenylphenylimino)ethyl]pyridine cobalt[II] chloride complex of the following formula:

Bianchini C., et al., Selective Oligomerization of Ethylene to Linear α-Olefins by Tetrahedral Cobalt(II) Complexes with 6-(Organyl)-2-(imino)pyridyl Ligands: Influence of the Heteroatom in the Organyl Group on the Catalytic Activity, Organometallics, 2003; 22:2545-2547, mention catalysts formed from certain pyridinimine ligands bearing appropriate substituents in the 6-position of the pyridine ring, cobalt dichloride (CoCl2), and methylaluminoxane (MAO). The catalysts are useful for oligomerization of ethylene (CH2═CH2) to give alpha-olefins. Also mentioned are certain cobalt salts or complexes such as, for example, a cobalt[II] chloride complex of the following formula:

PCT International Patent Application Publication Number WO 2008/112133 A2 mentions preparation of certain 2-imine-substituted pyridines as intermediates in the preparation of certain 2-aminomethyl-substituted pyridines as tridentate ligands to hafnium useful in preparing certain diblock copolymers, triblock copolymers, and multiblock copolymers from propylene and one or more copolymerizable comonomers other than propylene.
Chemical industry desires new processes of making trialkyl aluminum compounds in which at least one alkyl group is a primary alkyl derived from an internal olefin or alpha-olefin. Preferably, the new processes would employ isomerization/hydroalumination catalysts having improved stabilities and higher turnovers compared to those of pertinent commercial nickel catalysts such as, for example, bis(1,5-cyclooctadiene)nickel(0) (Ni(COD)2).